3-phenylthieno[3,2-b]thiophene | 35022-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并噻吩类
• 英文名称: 3-phenylthieno[3,2-b]thiophene
• 英文别名: 3-Phenylthieno[3,2-b]thiophene；6-phenylthieno[3,2-b]thiophene
• CAS: 35022-15-2
• 化学式: C₁₂H₈S₂
• 分子量: 216.328
• InChiKey: NUMJORFGVQWINX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylthieno[3,2-b]thiophene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯仿 为溶剂， 生成 2,5-dibromo-3-phenylthieno[3,2-b]thiophene
  参考文献：
  名称：

  使用噻吩并[3,2-b]噻吩和苯并噻二唑共聚物的高性能、低压有机场效应晶体管

  摘要：

  一系列新型线性共轭共聚物，以不同的取代噻吩并[3,2- b ]噻吩（TTs）作为供体，乙炔作为π-桥和苯并噻二唑（BT）作为受体单元，通过钯-催化 Sonogashira 交叉偶联聚合。这些共轭聚合物的光学、电化学和热性能通过以下方式进行评估紫外-可见、荧光、循环伏安法和热重分析。这些易溶的 TT-BT 共聚物被用作底栅顶接触 (BGTC) 有机场效应晶体管 (OFET) 中的半导体沟道材料。OFET 器件显示出 p 沟道场效应行为，并在 -3 V 以下以高产率成功运行。与具有芳族侧链的那些相比，包含具有脂肪族侧链的TT的聚合物材料表现出更好的OFET性能。使用带有壬基 (C 9 H 19 ) 侧链的噻吩噻吩的 TT-BT 的 OFET 在饱和状态下显示出最高的空穴平均载流子迁移率，μ sat = 0.1 cm -2 V -1 s -1，开/关电流比，I ON / I OFF = 3.5 ×

  DOI：

  10.1039/d2tc01222g
• 作为产物：
  描述：

  1-phenyl-2-(thiophen-3-ylthio)ethanone 在 polyphosphoric acid 作用下， 以 氯苯 为溶剂， 以84%的产率得到3-phenylthieno[3,2-b]thiophene
  参考文献：
  名称：

  可溶液加工的供体-π-受体型噻吩并[3,2-b]噻吩衍生物；合成、光物理性质及应用

  摘要：

  两种新型供体-π-受体 (D-π-A) 型拉-推材料M1和M2，以三苯胺作为供体，二甲基硼作为受体，通过噻吩并[3,2- b ]噻吩 (TT )通过用于 OLED 应用的溶液工艺合成和制造带有不同功能取代基（例如 -PhCN 和 -Ph）的 π-共轭间隔物。他们在固态和溶液中都表现出 120 nm 的兆斯托克斯位移和发射。单体M1和M2具有较强的分子内电荷转移行为；固态量子产率记录为 76% 和 72%，溶液量子效率分别确定为 100% 和 95%。溶液处理的 OLED 使用低开启电压制造，其最大功率、电流和外部量子效率分别约为 8 lm W -1、14.1 cd A -1和 4.78%，显示出蓝色的发射颜色为绿色和黄绿色。该材料在紫外线照射下具有介于黄色和蓝色之间的强烈荧光发射颜色。

  DOI：

  10.1039/d2tc02371g

文献信息

• Triphenylamine/4,4′-Dimethoxytriphenylamine-Functionalized Thieno[3,2-<i>b</i>]thiophene Fluorophores with a High Quantum Efficiency: Synthesis and Photophysical Properties
  作者：Recep Isci、Melis Unal、Gizem Kucukcakir、Naime A. Gurbuz、Sultan F. Gorkem、Turan Ozturk

  DOI：10.1021/acs.jpcb.1c09448

  日期：2021.12.9

  (TPA(OMe)2)-functionalized thieno[3,2-b]thiophene (TT) fluorophores, 4a–e and 5a–e, bearing different electron-donating and electron-withdrawing substituents (-PhCN, -PhF, -PhOMe, -Ph, and -C6H13) at the terminal thienothiophene units were designed and synthesized by the Suzuki coupling reaction. Their optical and electrochemical properties were investigated by experimental and computational studies. Solid-state

  一系列 10 种新型三苯胺 (TPA)/4,4'-二甲氧基三苯胺 (TPA(OMe) 2 )-功能化的噻吩并[3,2- b ]噻吩 (TT) 荧光团，4a-e和5a-e，具有不同的给电子和吸电子取代基（-PhCN、-PhF、-PhOMe、-Ph 和 -C 6 H 13) 在末端的噻吩并噻吩单元是通过 Suzuki 偶联反应设计和合成的。通过实验和计算研究研究了它们的光学和电化学性质。固态荧光量子产率记录为 20% 至 69%，最大溶液态量子效率达到 97%。此外，新型发色团的光物理表征显示出显着的斯托克斯位移，达到 179 nm 并具有红移。它们在溶液中表现出从橙色到深蓝色的调谐颜色发射，并显示荧光寿命达到 4.70 ns。三苯胺(TPA)/4,4'-二甲氧基三苯胺(TPA(OMe) 2 )-衍生的三芳胺与噻吩并[3,2- b]上不同官能团的关系] 噻吩单元进行了讨论。
• Oxidative Biaryl Coupling of Thiophenes and Thiazoles with Arylboronic Acids through Palladium Catalysis: Otherwise Difficult C4-Selective CH Arylation Enabled by Boronic Acids
  作者：Sylvia Kirchberg、Satoshi Tani、Kirika Ueda、Junichiro Yamaguchi、Armido Studer、Kenichiro Itami

  DOI：10.1002/anie.201007060

  日期：2011.3.1

  It adds up to 4! Thiophenes and thiazoles can be arylated in the 4‐ rather than the expected 5‐position in a new CH functionalization reaction (see scheme; TEMPO: 2,2,6,6‐tetramethylpiperidine‐N‐oxyl). The boronic acid proved to be the key to achieving the otherwise difficult C4 selectivity. The method was applied to a concise synthesis of a key pharmacological structure with potential for treatment

  总计为4！噻吩和噻唑可以在新的CH官能化反应中的4位而不是预期的5位芳基化（请参阅方案； TEMPO：2,2,6,6-四甲基哌啶-N-氧基）。硼酸被证明是实现否则很难的C4选择性的关键。该方法被用于关键药理结构的简明合成，具有治疗阿尔茨海默氏病的潜力。
• A General Catalyst for the β-Selective C-H Bond Arylation of Thiophenes with Iodoarenes
  作者：Kirika Ueda、Shuichi Yanagisawa、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1002/anie.201005082

  日期：2010.11.15

  less‐reactive β position of thiophenes was previously inaccessible to direct functionalization. However, the β selectivity observed with the catalytic system PdCl2/POCH(CF3)2}3/Ag2CO3 in the arylation of thiophenes with iodoarenes (see scheme) is a remarkably general phenomenon applicable to unsubstituted, monosubstituted, and disubstituted thiophene derivatives, as well as thiophene‐containing fused aromatic

  开放获取：通常无法直接将噻吩的反应性降低的噻吩的β位置进行直接功能化。但是，在噻吩与碘代芳烃的芳基化反应中，催化体系PdCl 2 / P OCH（CF 3）2 } 3 / Ag 2 CO 3所观察到的β选择性是一种显着的普遍现象，适用于未取代的，单取代的，和二取代的噻吩衍生物，以及含噻吩的稠合芳族化合物。
• Concise Syntheses, Polymers, and Properties of 3-Arylthieno[3,2-<i>b</i>]thiophenes
  作者：Asli Capan、Hojat Veisi、Ahmet C. Goren、Turan Ozturk

  DOI：10.1021/ma301604e

  日期：2012.10.23

  Thieno[3,2-b]thiophenes (TT), having pare-substituted phenyl groups at C-3, have been synthesized through a ring closure reaction, using P4S10, in moderate to high yields. Their absorbance studies displayed that the TT, having nitrophenyl group had the most red shift absorbance at 365 nm, which also showed the lowest optical band gap of 2.92 eV; the rest of the TTs had the absorbance between 300 and 302 nm. Cyclic voltammetry studies indicated that while all the TTs had the oxidation potentials above 1.0 V, the TT with dimethylaminophenyl group had the lowest oxidation potential of 1.33 V. The rest had the oxidation potentials between 1.6 and 1.99 V. The TTs were both electropolymerized and copolymerized with thiophene through Suzuki coupling reaction. Electropolymerized polymers indicated that while the polymer having strong electron donating dimethylaminophenyl group had the lowest oxidation potential of 0.97 V, the rest of the polymers displayed the potentials between 1.09 and 1.39 V. Their electronic band gaps varied between 1.86 and 2.46 eV. The CV-UV studies of the polymers, electro-deposited on ITO, showed absorbance maxima between 431 and 468 nm, and the lowest optical band gap was observed with the polymer having methoxyphenyl group (1.99 eV). The rest of the polymers had the optical band gaps between 2.05 and 2.19 eV. Regarding the copolymers, the one with methoxyphenyl group had the lowest oxidation potential of 0.75 V. They displayed absorption and emission maxima between 325 and 445 and 454-564 nm, respectively. Their optical and electronic band gaps varied between 2.0 and 2.5 eV. As the copolymer having strong electron donating methoxyphenyl group had the highest quantum yield, 0.64 eV, the one with strong electron withdrawing nitrophenyl group had the lowest quantum yield of 0.003 eV.
• High-performance, low-voltage organic field-effect transistors using thieno[3,2-<i>b</i>]thiophene and benzothiadiazole co-polymers
  作者：Bibi Amna、Recep Isci、Humaira M. Siddiqi、Leszek A. Majewski、Sheida Faraji、Turan Ozturk

  DOI：10.1039/d2tc01222g

  日期：——

  A series of new linear conjugated co-polymers, incorporating different substituted thieno[3,2-b]thiophenes (TTs) as the donor, acetylene as the π-bridge and benzothiadiazole (BT) as the acceptor units, were synthesized via palladium-catalyzed Sonogashira cross-coupling polymerization. The optical, electrochemical, and thermal properties of these conjugated polymers were evaluated via UV-vis, fluorescence

  一系列新型线性共轭共聚物，以不同的取代噻吩并[3,2- b ]噻吩（TTs）作为供体，乙炔作为π-桥和苯并噻二唑（BT）作为受体单元，通过钯-催化 Sonogashira 交叉偶联聚合。这些共轭聚合物的光学、电化学和热性能通过以下方式进行评估紫外-可见、荧光、循环伏安法和热重分析。这些易溶的 TT-BT 共聚物被用作底栅顶接触 (BGTC) 有机场效应晶体管 (OFET) 中的半导体沟道材料。OFET 器件显示出 p 沟道场效应行为，并在 -3 V 以下以高产率成功运行。与具有芳族侧链的那些相比，包含具有脂肪族侧链的TT的聚合物材料表现出更好的OFET性能。使用带有壬基 (C 9 H 19 ) 侧链的噻吩噻吩的 TT-BT 的 OFET 在饱和状态下显示出最高的空穴平均载流子迁移率，μ sat = 0.1 cm -2 V -1 s -1，开/关电流比，I ON / I OFF = 3.5 ×